When she went back to a more traditional sound with "Buckaroo," she didn't fare as well.
But she was at number 2 again the following year with the ballad "A Little Past Little Rock" and the more uptempo, fun sounding "I'll Think Of a Reason Later" from "Some Things I Know."
In 2000, Womack scored her greatest success with "I Hope You Dance," a career song for Womack. It stayed at the top of the charts for five weeks and won a Country Music Association award for single of the year.
The follow-up single "Ashes By Now" made it into the top five. Womack was touring heavily, opening for the likes of Alan Jackson.
All the effort managed to pay off with yet another award, female vocalist of the year in 2001 from the CMA.
Could Womack duplicate the success of an album that broke her as an artist and withstand the pressure?
Womack readily acknowledged feeling the squeeze. "The pressure I feel is how I deliver an album to the label that will be as commercially successful to the label and still satisfy me. That's the pressure I've felt from the first album."
In other words, there seems to be a dichotomy between the music that Womack loves - seemingly reflected in the more traditional honky tonk songs that she is comfortable with - and the more middle of the road music that is not exactly hard core country.
As to whether her fans understand what she's facing, Womack says, "I think they do. I feel more pressure of how we're going to get it (the music) to the fans. When you're on a major record label, the only way they know how to get it to the fans is on radio. I feel the pressure of satisfying my fans. I and I think my fans are more accustomed to the Buddy and Julie (Miller) and Bruce Robison style of songwriting. How do I please them and radio too?"
The Millers and Robison both are darlings of the edgy country crowd. Womack recorded songs from both previously - "Lonely Too" from Robison and "Does My Ring Burn Your Finger?" and "I Know Why the River Runs" from the Millers on "I Hope You Dance" and "Don't Tell Me" from "Some Things I Know."
This time out, Robison contributed "Blame It On Me," while Julie Miller penned the tough sounding "Orphan Train " and "I Need You."
The Miller songs clearly are tough sounding with a great deal of edge to Womack's voice, a far cry from her softer, more pop sounding songs.
"She'd already had cut one of my songs," says Robison in a phone interview from his Austin home. "But she's listening to my tunes. I thought that that was one that more commercial songs possibilities than most of the songs that I write. I sent it to her, and she liked it."
Womack says, "It's just one of those songs you listen to, and it breaks your heart. You can feel it."
But Robison's involvement didn't stop with writing the song. He sang harmony vocals as well.
"She's kind of a friend of mine, and he (Frank Liddell, the producer and Womack's husband) knows I'm a harmony singer," says Robison. "They called me about of the blue, and they asked me to come up there (to Nashville) and do it. I didn't ask any questions."
"Of all the people they could get, I was surprised, and I was happy, but I am a decent harmony singer. I sing a lot of harmonies, and I sing on (brother) Charlie's records, and it's just one of my things."
Womack says she enjoyed the experience. "It was one of the most pleasurable things I've done in making any of my records. Just because he's great at what he does, and I love working with people who are great at what they do."
Womack is well aware "Orphan Train" is different sounding and wanted to do it even though she figured her label would be scratching their heads.
The song has a spiritual quality about allowing the downtrodden to overcome their problems.
"I like the lyrics," says Womack. "I like what it said. I like the message of come all you broken hearted, come be a part of what we have going on. I just liked the song."
"I think it's real and honest and rootsy and raw," she says. "They (The Millers) make music from the heart and not from the pocketbook. To me, that's the way music should be paid. Unfortunately, most of the time it's not."
'Yeah I do," says Womack when asked if she finds that a difficult fact of life. "Because I have a record label that expects me to deliver music to them that will fatten their pocketbook. Not necessarily their heart. I understand that. It's a business. It's the music business. It's hard when you love music. It's hard to find that common ground."
"I'm sure they (MCA) weren't thrilled when I brought 'Orphan Train' in and 'Blame it On Me.'"
"They didn't really get the record until it was done," says Womack. "I wasn't necessarily sitting down with them and playing it either. I'm not saying they didn't like it. I'm sure they listened to it and thought we're going to have to work to get it on the radio. But you give them other things too like 'Something Worth Leaving Behind.'"